1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 4-(6-(5-(3-fluoro-2-(2-hydroxy-2-phenylpentylcarbamoyl)pyridin-4-ylthio)thiazol-2-ylamino)pyridin-3-ylamino)piperidine-1-carboxylate

HRID 1685353Notes

Reaction equation

HRID 1685353 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([NH:21][C:22]3[S:23][C:24]([S:27][C:28]4[CH:33]=[CH:32][N:31]=[C:30]([C:34](O)=[O:35])[C:29]=4[F:37])=[CH:25][N:26]=3)=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][CH2:39][C:40]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([OH:44])[CH2:41][CH2:42][CH3:43].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1.O>[F:37][C:29]1[C:30]([C:34](=[O:35])[NH:38][CH2:39][C:40]([OH:44])([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH2:41][CH2:42][CH3:43])=[N:31][CH:32]=[CH:33][C:28]=1[S:27][C:24]1[S:23][C:22]([NH:21][C:18]2[N:19]=[CH:20][C:15]([NH:14][CH:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH2:10]3)=[CH:16][CH:17]=2)=[N:26][CH:25]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 229923231-Amino-2-phenylpentan-2-olHCID 592004754-(2-(5-(1-(Tert-butoxycarbonyl)piperidin-4-ylamino)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid

Product 1

HCID 59200444Tert-butyl 4-(6-(5-(3-fluoro-2-(2-hydroxy-2-phenylpentylcarbamoyl)pyridin-4-ylthio)thiazol-2-ylamino)pyridin-3-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a stirring solution of 4-(2-(5-(1-(tert-butoxycarbonyl)piperidin-4-ylamino)pyridin-2-ylamino)thiazol-5-ylthio)-3-fluoropicolinic acid (586 mg, 1.072 mmol), 1-amino-2-phenylpentan-2-ol (479 mg, 2.672 mmol), EDAC (621 mg, 3.239 mmol), HOBt (235 mg, 1.739 mmol) in NMP (7 mL) was added i-Pr2NEt (0.93 mL, 5.339 mmol) and stirred overnight. LCMS showed complete reaction, which was poured into ˜50 mL water and a solid precipitated. The solid was collected by filtration, washed with water and was allowed to air dry. The product was obtained (838 mg, 100%) as a solid: LC/MS (M+H)+: 708. HPLC ret. time (Condition M): 1.95 min.

Workup

  1. customreaction, which
  2. customa solid precipitated
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customto air dry
  6. customThe product was obtained (838 mg, 100%) as a solid
  7. custom1.95 min.

Sources & evidence

ORD record
ord-8b431d7e4269476895e4166d6104d56f
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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